Privacy is of prime importance to many individuals when they attempt to develop online social relationships. Nonetheless, it has been observed that individuals' behavior is at times inconsistent with their privacy concerns, e.g., they disclose substantial private information in synchronous online social interactions, even though they are aware of the risks involved. Drawing on the hyperpersonal framework and the privacy calculus perspective, this paper elucidates the interesting roles of privacy concerns and social rewards in synchronous online social Interactions by examining the causes and the behavioral strategies that individuals utilize to protect their privacy. An empirical study involving 251 respondents was conducted in online chat rooms. Our results indicate that individuals utilize both self-disclosure and misrepresentation to protect their privacy and that social rewards help explain why individuals may not behave in accordance with their privacy concerns. In addition, we find that perceived anonymity of others and perceived intrusiveness affect both privacy concerns and social rewards. Our findings also suggest that higher perceived anonymity of self decreases individuals' privacy concerns, and higher perceived media richness increases social rewards. Generally, this study contributes to the information systems literature by integrating the hyperpersonal framework and the privacy calculus perspective to identify antecedents of privacy trade-off and predict individuals' behavior in synchronous online social interactions.